"Turn onto the McCauley Highway - none of the signs say that, but that's what it's called - go to the second light, where Zayre's used to be, then take the left - not the sharp left, but the other left, and it's 4 Dunkies and two more stoplights."

The layout shown there is midtown Manhattan which is based on the Commissioners Plan of 1811. This established the famous grid pattern. If you look at Lower Manhattan, the part which was heavily settled before 1811, it's considerably more bendy, although not nearly as much as Boston. But Boston has about half the population density of New York and less than a fifth the population density of Manhattan. It's also true that they picked one of the bendier parts of the city, outside of the North End and Financial District. Outside of the original peninsula, the denser parts of the city tend to be more gridlike, albeit without the nice ruler straight streets of Manhattan. If you look at Back Bay, the South End, South Boston, even Beacon Hill, these tend to be heavily gridded areas. It's only when you get out into areas like Dorchester, Roxbury, and Brighton, which were all more rural areas annexed to the City in the 1800s, that you tend to see abundances of curvy crazy streets. Again, downtown is the exception, but that was settled in the early 17th century and was a narrow strip of land until the 19th. Anything built on landfill has a general straightness to the streets, although not always a nice grid pattern. And even in Dorchester, there's an attempt to make a lot of the streets more or less straight. Zoom in on a google map and you'll see lots of basically straight streets, although, again, not in a nice grid pattern and not ruler straight.

But most Bostonians live in Crazy Street World (my favorite Boston grid is in Hyde Park - there's A Street and B Street and then they just gave up). Also, we have the fun of having several Mt. Vernon streets, a couple of LaGrange Streets, 4,000 Washington streets, etc.

True but it's less dense is the point. The grid is more or less a necessity for dense cities because it lets you pack in large numbers of people and simplifies property lines. But Roxbury, Dorchester, Brighton, Roslindale, these are all former outlying farm communities which were annexed to the city in the 19th century. These were, and are, less densely populated regions than the core of the origin city or the areas built on landfill (South Boston, Back Bay, East Boston) and so they have they will have fewer roads built along grids. Remember, much of these neighborhoods are considerably more suburban in nature than the denser inner core of the city, with single family detached houses and yards often being the norm. Comparing them to Manhattan, the densest county in the country is more than a little misleading. Remember also that most of Americans live in suburbs, not cities. Rather than viewing the Commissioners Plan of 1811, which is so formative that it's still remembered 200 years after it was issued (and treated as a proper noun no less), as being normal it should be recognized as being exceptional in the American experience. The grid was highly unusual for American settlements at the time, and while many cities came to adopt variations on the grid pattern, these tend to be for the denser parts of the city. The further you move out the more bendy the streets become. Google just about any suburb in America and you'll find lots of bendy roads and very few grids in sight.

By the mid-1800s, new cities were laid out ahead of time. There was a constant tug-o-war between the Clackamas County courthouse in Oregon City, Oregon and San Francisco, CA over where the original street plan maps for SFO should reside.

The point being that they laid out the street grid of the city well before they actually built it, and that this was required for it to be a city and had to be drawn up and filed.

These original maps were in Oregon City because that's where the Oregon territorial government was headquartered before northern California was split off and added to Southern California and then became a state.

Boston, which started growing in size and importance sometime in the late 17th century grew like most European cities.

Boston has a lot in common with typical European cities, less with other North American cities.

And Boston is still the 3rd most densely populated big city in the U.S. after NYC [by far #1] and S.F. which Boston is similar to. Cambridge, Somerville, Chelsea are even on average more densely populated than the City of Boston. I've been to many big U.S. cities and lived in L.A. for a while. Almost all of southern and western cities have considerably less population density than Boston and few other northern cities. And they are VERY spread out, like giant suburbs. Atlanta is 130-odd square miles in land area with a population of around 430,000. Boston is 48-odd square miles in land area, with a population of 625,000. Add just Brookline, Cambridge, Somerville, and Chelsea [total land area around 18 square miles, population 273,000] and you've got 900,000 people in 66 square miles, still CONSIDERABLY smaller geographically than most big U.S. cities. The City of Houston [4th largest city in the U.S.] is 600[!] square miles in land area with 2.1 million people, a population density of a little over 3000 people per square mile, less than the typical inner suburb of Boston, let alone Boston itself.

The North End is the most densely populated part of Boston and it's not a grid, just well-connected with small blocks.

Paris and London are similar. And in Tokyo, forget about street addresses entirely, they don't exist.

Go look at places like Chicago or Phoenix, their grid extends far out into many suburban areas (though not all). Or they'll have a large-scale grid and inside that either a smaller-scale grid, or some other arrangement at the fine-grain level. Much of the western US was surveyed along grid lines on a map, so it was quite natural by the time the cities there were developed.

Olmsted favored curving roads and following terrain, and his influence on suburban development is probably what resulted in this "lower density / bendy street" correlation that we observe.

Although grids are good for connectivity, they aren't strictly required for that. Old places that were built up when the primary mode of transportation was walking generally feature small blocks, small streets, good connectivity, but do not necessarily have grids.

Some do. Kyoto famously has a grid -- it even features in The Tale of Genji written about a thousand years ago. That was a planned city though -- the name even means "Capital City."

I've lived in some very rural, <5000 person "cities" in my life and they all had grid systems.

Just a matter of whether or not there was initial planning for expansion and design for laying out of services and roadways ahead of time - even if only on paper.

Again, this has a lot to do with the era of founding and initial development. Some of that is related to whether railroads, rivers, or road travel was dominant at the time. New England has more of a grow-as-you-go hub and spoke setup based on roadway travel.

I particularly like the sign on the south shore: 95 South/128 north, or visa versa. Or how about no signs off 93 at the 128 junction actually saying this exit for 128? I can't tell you how many times out of state/area visitors get lost to my home.

In my experience locals are kinder to strangers in NYC than they are in Boston. Perhaps this is why I get stopped and asked for directions so often on the T--I look like I'm from out of town but also like I know where I'm going.

Logan INTERNATIONAL Airport bothered to even have dedicated signs for the MBTA shuttle buses and Silver Line (including which of the numbered buses to take where ...), information in an obvious well-signed place, and well signed roadways that get people in the correct lanes in case they want to get somewhere other than downtown Boston for starters ...

Bonus fun NYC grid fact: Brooklyn's also built on a grid, but back in the old neighborhood are a few streets that break the grid - because they're remnants from the grid the Dutch were building - which didn't run at the same angles as the one the English and Americans built.